ArticleChemical science2019
Visible-light-induced intramolecular charge transfer in the radical spirocyclisation of indole-tethered ynones.
Article in Chemical science, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed.
- Visible-light-promoted photoredox synthesis of thioacetylenes by dehydrogenation coupling of thiophenols and alkynes.RSC advances · 2025Article
- Vibrational Spectroscopic and Quantum-Chemical Study of Indole-Ketone Hydrogen-Bonded Complexes.Molecules (Basel, Switzerland) · 2025Article
- Visible-Light-Induced Dearomative Annulation of Indoles toward Stereoselective Formation of Fused- and Spiro Indolines.ACS omega · 2024Review
- Photochemical dearomative skeletal modifications of heteroaromatics.Chemical Society reviews · 2024Review
- Shining light on tryptamine-derived isocyanides: access to constrained spirocylic scaffolds.Chemical science · 2024Article
- Photo-induced imino functionalizations of alkenesChemical science · 2023Article
- Combining photoredox catalysis and hydrogen atom transfer for dearomative functionalization of electron rich heteroarenes.Chemical science · 2023Article
- Copper-catalyzed oxidative dehydrogenative dearomatization of indole derivatives: A new strategy to construct spirocyclic indolenines.iScience · 2022Article
- PIFA-mediated selenylative spirocyclization of indolyl ynones: facile access to selenated spiro[cyclopentenone-1,3'-indoles].RSC advances · 2022Article
- Highly congested spiro-compounds via photoredox-mediated dearomative annulation cascade.Communications chemistry · 2022Article
- Selectivity, Speciation, and Substrate Control in the Gold-Catalyzed Coupling of Indoles and Alkynes.Organometallics · 2022Article
- Allene TrifunctionalizationThe Journal of organic chemistry · 2021Article
- A Thiol-Mediated Three-Step Ring Expansion Cascade for the Conversion of Indoles into Functionalized Quinolines.Organic letters · 2021Article
- Synthetic reactions driven by electron-donor-acceptor (EDA) complexes.Beilstein journal of organic chemistry · 2021Review
- Thiyl Radicals: Versatile Reactive Intermediates for Cyclization of Unsaturated Substrates.Molecules (Basel, Switzerland) · 2020Review
- Synthetic Methods Driven by the Photoactivity of Electron Donor-Acceptor Complexes.Journal of the American Chemical Society · 2020Article
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Authors and funding
10 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Indole-tethered ynones form an intramolecular electron donor-acceptor complex that can undergo visible-light-induced charge transfer to promote thiyl radical generation from thiols. This initiates a novel radical chain sequence, based on dearomatising spirocyclisation with concomitant C-S bond formation. Sulfur-containing spirocycles are formed in high yields using this simple and mild synthetic protocol, in which neither transition metal catalysts nor photocatalysts are required. The proposed mechanism is supported by various mechanistic studies, and the unusual radical initiation mode represents only the second report of the use of an intramolecular electron donor-acceptor complex in synthesis.
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Registered trials
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